Could Have, Should Have, I'm Glad I Did That
by SeraphimDarkholme
Summary: While the Enterprise is being repaired on Earth, Kirk drags Bones away from work and self loathing to work on a recruiting mission that will turn Bones' life upside down. Rated T for potty mouths! Leonard H. McCoy X OC
1. Chapter 1

**Could Have, Should Have, I'm Glad I Did That**

_Disclaimer: I do not own Star Trek; I do not own the Gene Rodenberry, or the J.J. Abrams version. This is the J.J. Abrams version, but again I do not own Star Trek or anything affiliated with Star Trek or the before mentioned Parties. This is a work of pure entertainment and I am not making any profit from this. The characters belong to Gene Rodenberry and J.J. Abrams and are their respective properties. Please do not sue me._

Bones looked at his medical reports and sighed.

"Maybe I should have been an engineer," He said to himself as he pinched the bridge of his nose. "I would still get to use my hands and fix things, but at least the things I fixed wouldn't talk back."

He got out of his chair and stretched his legs. Hours of sitting down after hours of standing up and running around like a maniac all day tends to wear one down very quickly. He walked over to the food synthesizer and punched in a request for coffee. The synthesizer beeped and asked him to further specify his request.

"Coffee, dark roasted blend, on a strength scale of one to eight I want an eight, two creams, two sugars," He said sighing at the annoying routine he has started with the machine. "Specification end."

The machine synthesized a cup of coffee and he sat back down. He allowed his eyes a brief moment of rest before beginning his work again. After two more hours of reading, commenting, taking notes, and scheduling appointments his communicator beeped.

"Captain Kirk to Chief Medical Officer McCoy," Kirk chirped. "I need you to visit Admiral Pike. He wants us to help him recruit for Starfleet."

"Damn it Jim," Bones replied tiredly. "You know that I'm not using this shore leave to lolly gag like you are! I'm actually working my ass off!"

"But Bones," Jim replied with a fake whine. "It's for a good cause."

"And what pray tell is so good about this cause?" Bones snipped at Kirk.

"We're encouraging youth to make something of themselves?" Kirk replied with a will you buy that tone.

"Where is the recruitment going to be?" Bones asked bracing himself for the headache the answer would give him.

"A local college," Kirk replied with a happy tone. "Think about it Bones, some of the kids will drop out and at least we'll give them an option."

"Jim," Bones said putting his PADD down. "I'm going to say yes, only because you (a) probably already told Pike I said yes, and (b) I have to make sure that when those college girls' jealous boyfriends come after I'll have a good view of them kicking your ass."

"We leave at 0700 hours." Jim said in such a way that Bones could tell that Jim was wearing his signature shit eating grin.

"Wipe that damn smirk off your face!" Bones said cutting the communication link.

He leaned back in his chair and wiped his face.

"I could have gone to Ole Miss to be an engineer, but no," He mused as he turned his attention back to his reports. "I had to be noble and want to cure the sick. I had to save the world from the germs and diseases the universe has to throw at the galactic populace, now look where I am. I'm divorced, I haven't seen my kid in almost four years, and I'm now a poster boy for Starfleet. A- freaking- mazing."

Five hours passed and now he was finally finished with his reports. He gave a small grin at his handiwork and stood up and stretched before looking at the clock and saw that it was 1900 hours. He had literally spent all day working on his reports, but he had finished them.

"Well now that that is done, time for some dinner," He said walking over to the food synthesizer. "One sandwich, turkey, lettuce, tomato, red onion, pickles, black olives, provolone cheese on whole grain bread with oil and vinegar please."

After a few moments of processing his request the machine produced the sandwich. He took a bite of the sandwich and gave a grunt of mild approval. It wasn't as good as a real homemade sandwich, but he was so hungry he would have eaten his boot if he could. He was about to take another bite of his sandwich when his door alarm beeped.

"Open up Bones," Kirk said giving the door a couple of knocks. "I know you're in there! All you ever do is stay in your damned room!"

Bones rolled his eyes.

"Enter." He said watching Jim enter the small apartment with twinkling eyes. "Whatever has happened Jim, I really don't want to know about it."

"Nothing has happened, yet," Jim said smiling as he watched Bones eat his sandwich. "But there is a small restaurant that serves really good beer just down the block."

"Jim," Bones said slowly. "I've told you this, I am not spending my time on Earth in bars, I have just finished a huge load of reports on various members of the crew, I had to write out death certificates yesterday, and I had to patch you up because you picked on Lieutenant Cupcake again! I'm tired Jim! I just want to rest!"

Jim looked thoughtfully at Bones for a moment.

"Beer helps you relax." Jim said trying to look serious.

Bones sighed and looked at his friend.

"You're not going to leave until I say yes, are you?" Bones asked tiredly as he finished off his sandwich.

"Nope," He said grinning. "I'm going to sit here until you say yes."

"Damn infant." He said standing up and stretching again. "Let me throw something half decent on, I can't go out wearing my pajama pants and a worn out Ole Miss sweat shirt."

"At least you can't be arrested for wearing you night clothes out in public," Jim said stuffing his hands into his pockets. "Not like I was."

Bones turned to his friend and quirked his brow.

"You were arrested for wearing you pajamas in public?" Bones asked incredulous.

"Well sort of," Jim replied with a grin. "I sleep naked."

Bones rolled his eyes and went into his bedroom to get dressed. He looked at himself in the mirror and sighed. He didn't shave this morning and it showed. It made him look older than he really was, but then again the worry lines and the crows' feet didn't help him out either. He was going to shave when Jim began banging on his door.

"Forget the shaving part," Jim said obnoxiously. "We're just going to get beer, it's not like we're meeting the freaking royal family of Betazed."

Bones sighed as he pulled on a pair of jeans and a t-shirt.

"I'll be out in a moment you damned infant!" He snapped back as Jim continued to bang on the door.

He grabbed his jacket and opened the door. Jim stood there tapping his foot in mock impatience.

"Finally decided to join the rest of the world Bones?" Jim said in fake frustration.

"If the rest of the world acts anything like you," Bones said putting his jacket on. "Then I think I'll stay in my room forever!"

"Now who's being the infant?" Jim asked poking his elbow into Bones' side.

"Damn it Jim!" McCoy said looking at Jim. "Are you soused already?"

"Nope," Jim said hailing down a cab. "I'm not drunk, yet."

Bones looked at Jim and frowned.

"I'm not getting drunk Jim!" Bones said as a cab finally stopped for them. "I still have stuff to do tomorrow and what kind of example would we be setting if we showed up to a recruitment mission drunk?"

"The kind that says Starfleet is not all about business." Jim replied smiling like an idiot.

"You're a damned idiot." Bones said getting into the cab. "And since you're dragging my tired ass out of the apartment, you're paying for the fare!"

"Blah, blah, blah," Kirk said shoving McCoy as he got into the cab. "Take us to El Stallion please."

As the cab drew closer to the restaurant Bones began to realize something.

"You're taking us drinking in one of the campus bars!" Bones said loudly.

"Relax," Jim said patting his friend on the shoulder. "We're just staking out the territory and seeing what we're dealing with."

"You're an asshole!" Bones said throwing punches at Jim's nearest arm.

"Hippocratic oath," Jim cried as he tried to block the blows. "You can't kill me!"

Bones got this maniacal look in his eyes.

"I'm not in uniform Jim," Bones said still hitting Jim. "And I'm off duty! I can kill you if I feel like it!"

Bones was going to go for Jim's head when the cab stopped.

"We're here now get the hell out of my cab," The driver said sourly. "I got kids that act better than you two do."

Jim paid the driver and they walked into the restaurant and to Bones dismay, Pike was in on the little scheme too.

"Good evening gentlemen," Admiral Pike said smiling as he rolled up to them. "Captain Kirk and I have arranged to meet with a very interesting group of students. Please follow me."

Pike led them to a large round table with three people seated already.

"Kirk, McCoy I would like you to meet Eric Marsters, Wynifred Bates, Sharlek Tanner, and, Ms. Ryan still isn't here?" Pike said slightly annoyed.

"She said she's on her way," Wynifred said looking at her phone. "The guy she's tutoring is starting a Vulcan Math and he needs a little extra help."

"Oh well that's excusable I suppose," He said nodding. "Let's go ahead and order. I called you all here to talk to you about joining Starfleet. Your aptitude tests were beyond excellent and you have shown great potential as leaders—"

A young woman with short brown hair, brown eyes, and wearing a leather jacket rushed up to the table.

"Sorry I'm late sir," She said extending her hand to Admiral Pike. "I got caught up with my pupil, but at least he understands the importance of dimensionality."

She sat down in front of Bones and he saw her labret lip ring, her nose ring, and her small gauged earrings.

Admiral Pike smiled.

"And last but certainly not the least of our outstanding group, Jane Ryan, Education Major, engineering minor." Admiral Pike said smiling in her direction.

"I hardly need introduction sir," She said taking a bottle of tequila and a lime from the waiter. "I ordered this on my own, pass the salt please, I don't like being bragged on, it makes me feel over glorified."

Bones watched as poured a shot of tequila into a shot glass, licked her hand, and poured some salt on it.

"You're a teacher?" Bones said slightly horrified as he watched her down the shot of tequila, lick the salt, and eat the lime. "Do they just let anybody teach?"

She opened her eyes and looked at him.

"Don't fuck with me Leonard Horatio McCoy," She said shaking her head. "I do my job and I do it well, and I'll be damned if I'm going to take lip off of you!"

Bones looked at her for a moment and realized she had a southern drawl.

"With an accent like yours I'm surprised your momma hasn't whooped your ass yet for having those things in your face!" Leonard snapped back.

"She doesn't pay for my education," Jane replied taking another shot. "I do. She can't tell me shit, I'm here in San Francisco and she's in Southville Georgia."

Jim clapped his hands together and smiled.

"Tequila sounds like a great idea! Shots are on me!" He said trying to calm the fire.

"Damn it Jim," Bones said tiredly. "I told you I'm not getting drunk!"

"I'm not saying let's get drunk. I'm just saying a shot around the table." Jim said trying to keep tempers in check.

"I say she's taking enough shots for us all!" Bones said pointing to Jane.

"Piss off!" She said taking one more shot.

"You first!" Bones shouted angrily.

"Do us all a favor and get that stick surgically removed from your ass!" She said standing up. "I'm sure your crew mates would appreciate it!"

"Is that a fact, Miss Over Compensation," Bones said getting in her face. "I'm sure that all those metal bars in your face must attract all the guys. They appear to be lining up to see you and your pierced glory, your lesbian haircut, and butch biker jacket!"

The three students saw the rage in her eyes. She looked at him grabbed the bottle of tequila poured another shot and took it without lime or salt. She found the bottle top and screwed it on tightly.

"I'm going to let that slide considering your ex-wife fucked you over in your divorce," She said keeping her voice calm and cool. "But the next time you ever insult me like that, I will beat the living hell out of you."

She placed the capped bottle on the table and walked out.

"You guys can have the rest." She said walking away.

"Good job Bones," Jim said slapping his friend on the back. "You're just a few centimeters away from getting your ass kicked by the most damaged person on the entire campus."

Bones looked around the table.

"Damaged?" He asked looking at everyone.

"Yeah," Wynifred replied. "Her mom and stepdad only call her if they want money, she works part time, goes to class full time, attends three different clubs, tutors people with learning disorders, and her grandparents and brother died in a shuttle crash three weeks ago. She acts like it doesn't bother her, but we can all see she thinks its her fault their dead."

Bones wiped his face and realized how stupid what he did was.

"How can she think that a shuttle craft crash was her fault?" He asked pouring himself a shot of tequila.

"They were coming to visit her." Wynifred replied watching McCoy take a shot. "And if I were you I'd give her a day to cool off. When she's pissed she's likely to bite your head off before giving you a second glance."

Bones sighed and motioned for Jim to move.

"I'm calling a cab home," He said looking at the group. "I've made enough of an ass of myself without getting drunk. Sorry about the outburst. Good night."

Jim sighed.

"Great," Jim thought to himself. "Now Bones is depressed too."

The trip back to the apartment seemed to take forever compared to the trip to the restaurant. He felt his guilt and his conscious eating away at him like nothing he's ever experienced. He should have thought before he spoke but she set off some kind of spark that lit his fuse. He should have known better to let it blow like he did.

"Well Bones," He said pouring himself a glass of scotch. "Here's to screwing up, something you're good at."

After he emptied his glass he took a shower and went to bed.

"Tomorrow's a new day," He said as he laid his head on the pillow. "And I can always apologize for being a complete ass, right before I act like a complete ass again."


	2. Chapter 2

**Could Have, Should Have, I'm Glad I Did That**

_Disclaimer: I do not own Star Trek; I do not own the Gene Rodenberry, or the J.J. Abrams version. This is the J.J. Abrams version, but again I do not own Star Trek or anything affiliated with Star Trek or the before mentioned Parties. This is a work of pure entertainment and I am not making any profit from this. The characters belong to Gene Rodenberry and J.J. Abrams and are their respective properties. Please do not sue me._

Jane staggered her way back to campus, a few people tried to bother her, but drunk or not, she had a good arm. She finally made it back to her dorm when Sabrina, the campus idiot, walked up.

"Jane are you drunk?" Sabrina asked narrowing her already beady eyes. "You know you're not supposed to have alcohol in or on you on campus. Are you stupid Jane?"

Jane grunted and stumbled her way to a turbo lift with Sabrina in tow.

"You're going to have a hangover," Sabrina continued on the turbo lift. "Then the recruiters won't want you."

"Shut up." Jane said through grit teeth.

"Huh?," Sabrina replied. "I had a cousin who had a hangover when he applied to Starfleet and they wouldn't let him in because he had a hangover, which was bad because his girlfriend left him for another woman, and later that day his dog had to be put to sleep and-"

"SHUT. UP." Jane said loudly. "I don't care. You're life is always more tragic than everyone else's! Hamlet has nothing on you does he? No, of course not that would mean he would be taking attention away from you!"

Sabrina looked at Jane stunned. Jane was always calm and cool and collected and never shouted at anyone even if they did need it.

"I'm just telling you what happened." Sabrina said as her thin lips curled into and indignant frown.

"Shut up! I don't care," Jane said staggering to her room. "Everyone knows every disgusting detail about your life! I can't tell you how many times I've had to hear it!"

"I'm sorry my life is so horrible to hear about!" Sabrina said mustering up fake tears.

"Don't try those damned crocodile tears. Everyone knows about them. I refuse to feel sorry for you! All you do is tell people how horrible your life is and how many times you were struck by lightning and how many cars have hit you and how many miscarriages you have had! You've drained your sympathy dry! There is none left! Go FUCK YOURSELF!" Jane yelled reaching her room.

Jane opened the door and Sabrina looked at her.

"If that's the way you feel then we can't be friends anymore!" Sabrina said over dramatically.

"Good fucking riddance!" Jane shouted laughing hysterically.

Jane slammed the door and smiled.

"One less asshole to deal with!" She said walking over to her bed and passing out.

* * *

><p>Bones woke up the next morning and groaned.<p>

"I should have got drunk, I wouldn't have to remember what I did last night, I'd just be in pain." He said to himself as he got up and walked to the bathroom.

After using the toilet he took a hot shower and then he shaved and brushed his teeth. He then noticed how much younger he looked once the stubble and hair was gone from his face. He shook his head and laughed at how superficial he was being. He put on his uniform and stepped out of his room to see Jim waiting for him.

"Can't call ahead like normal folk can you?" Bones said with a frown.

"Bones," Jim said smiling. "If I ever did anything by the book that would be boring."

"Infant." Bones said walking towards the turbo lift.

"Wah." Jim said in a fake baby cry. "Find me a woman, I'm hungry."

"Only you can turn something as innocent as nursing into something dirty." Bones said shuddering slightly.

"Well," Jim replied quirking his brows. "I'm not the only one who can, I'm just the only one brave enough to do it around you."

"I hate you." Bones said straightening his shirt.

" I love you too Bones." Jim said as they stepped off the turbo lift.

"When does this thing end?" Bones asked as they walked up to the cab.

"About 1230 hours." Jim said smiling at Bones' eye rolling.

"You owe me one hell of a lunch," Bones said folding his arms. "If I have to deal with melodramatic teens and twenty-somethings all day, I'm gonna at least get lunch out of it!"

"Bleh, bleh, bleh!" Jim said rolling his eyes as his friend complained.

"Jo Anna is more mature than you and she is six." Bones complained.

"Shut up and enjoy the sights of scantily clad college girls." Jim said smiling as the cab drove past two blondes.

"Jim they're almost half my age." Bones protested as they passed a group of bikini clad girls on their way to swim class.

"You're mouth says no," Jim said watching Bones. "But your eyes shout I wanna tap that!"

Bones looked at Jim.

"Did I forget to mention I hate you?" Bones asked with a sarcastic tone.

"Aw! Bonesy," Jim said smiling. "You only tell me every chance you get."

"We're here," The cab driver said. "Have fun."

"Don't worry," Jim said swiping his card. "We will."

"Fun my ass." Bones said straightening his shirt once again.

"If you straighten your shirt one more time you anal-retentive badger I'm personally going to glue it straight." Jim said trying not to laugh.

"Keep it up and I'll make so that the dermal regenerator "accidentally" puts some skin over your lips." Bones quipped back.

Admiral Pike rolled up.

"Good morning gentleman," Admiral Pike said with a slight smirk. "I take it you are having an intellectually stimulating converstation."

"As a matter of fact sir," Jim said with his signature grin. "We are, Dr. McCoy here was telling me about a fascinating use for the dermal regenerator."

Pike quirked a brow and looked at McCoy.

"I can tell he has a few extra uses in mind right now," Pike replied with a grin. "Come on I'll show you the way to the auditorium."

Bones and Jim followed Pike to a large auditorium.

"You and Dr. McCoy will be taking questions. I'll do all the talking." Pike said with a small smile. "Any questions?"

"Yeah," Jim said watching some girls pass by. "Can I keep one?"

Bones rolled his eyes and looked at Pike.

"You wouldn't happen to have a hose I could borrow do you?" Bones asked looking at a drooling Jim.

"Just try to keep him out of trouble." Pike said rolling away.

"Easier said than done," Bones said grabbing Kirk. "Come on!"

* * *

><p>Bones stood and listened to Pike go on about how great Starfleet was and about how it was a peacekeeping armada. He told students how Starfleet helped him and how he enjoyed praticing medicine. He had never done it before but it already felt routine to him.<p>

"So," Pike said enthusiastically. "If there are no more questions, you can begin sign up now!"

Jim was relishing the attention all the girls and some guys were giving him, but all the girls seemed to remind Bones of Jocelynn. They all seem to have an air of look at me about them. They draw attention to themselves to be noticed. They scream future trophy wife. They wanted to be trophy wives, they were here for dupes like him, dupes who wanted to have the hot wife, dupes who would fall for their lies. He was about to think of more when a familiar voice broke his thought.

"So if I sign up do I have to deal with you?" Jane asked looking at him from under her sunglasses.

"Nope. It's a sign on bonus," Bones replied sarcastically. "Sign up with a hang over and you don't have to deal with me."

She had what he could tell must have been a blank look on her face.

"Listen kid," He said sighing. "I'm sorry about last night-"

"Don't regret anything," Jane said signing her name on a PADD. "Regretting things only make you older and bitter."

Bones looked at her for a moment and sighed.

"Am I forgiven or what?" He asked testily.

She gave a lopsided grin and made a preistly gesture with her right hand.

"You are absolved my child." She said in a mock priestly tone.

Bones gave a small grin.

"Good," Bones replied smiling. "Now I can go to hell for thinking that was funny."

"I'll save you a seat," Jane said smiling. "And the name is Jane, not kid."

She smiled at him before walking off in her leather jacket. Bones smiled as he watched her leave. She was one of the few who came for her and only her and not to get their Mrs. Degree. Also she did know how to rock a man's leather jacket.

* * *

><p>Pike smiled at Bones and Jim after the recruitment was over.<p>

"Boys you did a good job, Jim, I'm especially proud of you," Pike said with a playful smirk. "You only got hit three times today."

Jim quirked his brows sarcastically and Bones rolled his eys.

"Thank God though I was there to stop the fights or else he would have more than a shiner!" Bones grumbled.

"My hero!" Jim said dramatically throwing his arm over his head.

"Infant." Bones replied grumpily.

"Wah." Jim said rubbing his growling stomach. " I was promised food if I helped recruit."

Bones looked at Jim increduouls.

"Wait," Bones said folding his arms. "Jim promised me food, and you promised him food and the view of college girls. I guess it is true. The human psyche can be broken down into two things: food and sex."

"Two out of three of my favorite things." Jim quipped with a smile.

Bones sighed and pinched the bridge of his nose.

"I'm gonna regret asking," Bones said sighing. "But what is your third favorite thing?"

"Booze." Jim replied smiling as he held up three fingers. "Sex, food, and booze are a few of my favorite things."

"Start singing and I kill you," Bones said folding his arms. "Hippocratic oath or not."

Jim let out a laugh which prompted an amused sigh out of Pike.

"Hate." Bones said drawing the word out as long as he could.

"Yeah, yeah, yeah!" Jim said moving his hand in an up and down motion. "I want food! I was promised food!"

"You are an infant!" Bones said dodging Jim's yapping hand.

"You're both acting like children," Pike said rolling toward a cab. "Keep it up and you won't get dessert."

Bones rolled his eyes and Jim pouted.

"Where are we going?" Bones asked as he helped Pike into the cab.

"A small Italian restaurant on campus," Pike replied as Jim crawled over him. "It comes highly recommened, damn it Jim, do you have to crawl over me with your filthy boots?"

Jim smiled at him and nodded.

"Jo Anna. Six. More mature than you." Bones said closing the trunk and sliding into the seat next to Jim. "Who recommended it?"

"Some of the students," Pike said watching Jim watch girls. "Wynifred said it served really good lasagna."

"Italian is some of the most unhealthy stuff you can eat!" Bones said folding his arms.

"That's why it's good." Jim said fidgeting. "I hate sitting in the middle."

"Then why did you take the middle seat!" Bones said frustrated by his friend's infantile behavior.

"I wanted to sit next to both of you." Jim said smiling like a silly toddler.

"Again, I would like to reiterate, Jo Anna is six years old and is years more mature than you are." Bones said looking out the window. "If this is the restaurant, it's packed."

"Don't worry," Pike said smirking. "I've got us a seat."

* * *

><p>Wynifred sat with Jane at a large table in the crowded restaurant.<p>

" I cannot believe you told her off!" Wynifred said in shock.

"So she's already trying to siphon sympathy?" Jane replied sipping a martini.

"What were you thinking?" Wynifred replied incredulous. "You know how she is about people being mean to her-"

"Let me understand this," Jane said holding her hand up in Wynifred's face. "Sabrina, can dress herself like a cheap hooker and tell me what to wear, but I can't tell her to put clothes on, Sabrina can put make up on like a two cent slut and tell me that I need to wear make up and when I do wear make up she gives me attitude about wearing it! I can have my life fall apart before my eyes, but don't worry, she has a worse story about her two or more miscarriages, her getting hit by fucking cars, and striken by lightning! I'm sorry if I'm sick of never being able to have a thought with out her crawling into my brain and telling me how bad off she is! I can't even mourn without her telling me how bad her pain is! LET ME HAVE MY FUCKING MOMENT OF SILENCE!"

Wynifred stared at her friend wide eyed. She knew Sabrina had pushed Jane's buttons, but she didn't realize how badly. She wanted to say something, but she knew better and she just stayed silent. Jane had been through a lot, but she never took the time to understand that no one had allowed her to mourn. She watched with a slight twinge of guilt as Jane ordered another martini. She was about to tell Jane she was sorry when Admiral Pike rolled up.

"Admiral!" Wynifred said putting on a happy face. "I'm glad you could make it, we're here to discuss our options."

Bones saw Jane sitting at the table with a distant and bitter look on her face. A look he had seen many times in the mirror. He had seen anger, resentment, depression, and loneliness in his own face enough to know that the same emotions he use to feel and still did feel was running deep with in her. He was shaken back to reality when the waiter bumped into him.

"I'm sorry sir." The waiter said turning to him smiling before handing Jane another olive martini.

Jim noticed Bones and nudged him.

"If you're not going to move, then I'll get in," Jim said sliding in next to Jane. "I'm starving!"

"They have excellent lasagna!" Wynifred said happily. "Don't you think so Jane?"

"I like the calzones." Jane said taking a sip of her new martini.

"I think I'll just have a salad," Bones said flipping his menu over. "I don't need any of this heart attack inducing food."

Jane looked at Bones over her martini and put it down.

"You're going to eat at an Italian restaurant and order a salad?" She asked putting the glass down.

"I don't want to die of clogged arteries," Bones said in his usual snark tone. "I like being alive."

"What's the point of living if you only make yourself suffer," Jane said picking her glass back up and taking a sip. "The meaning of life is to live, not exist. Live means doing all you can to the best of you ability **and **enjoying what you do; however , to exist means to trudge about hating your life and wishing that you would had or hadn't done things in your life. Try something new. Eating a calzone once **will not** kill you."

Bones looked at her for a moment and wanted to reply with a smart ass remark, but he couldn't. He saw an unnatural age in her eyes that said don't doubt me.

"Fine," He said in a snippy tone. "I'll try a damned calzone. I should have a salad, but who care that I could have a heart attack!"

Jim rolled his eyes and prayed that Jane wasn't intoxicated too heavily.

"If you do have a heart attack Dr. McCoy," Jane said smoothly. "I'll wear red to your funeral and bury you in a white suit with a guitar."

"Jane!" Wynifred said in shock. "I think you've had enough."

Jane shrugged as she looked at Bones.

"White suit?" Bones replied looking at her. "Not after Labor Day I hope."

Jane smiled and slightly tipped her glass toward him.

"Always after Labor Day." She said taking a sip.

* * *

><p>Bones wiped the crumbs off his face and sighed.<p>

"That was good," He said trying to hide his satisifaction. "I'm glad I did that."

Jane smiled and sighed.

"I'm glad too," She said nodding. "Now I don't have to hear you complain."

Pike smirked.

"So," Pike said clapping his hands together. "You ladies are accepted, but the only question left is when do you want to come?"

Wynifred whisped to Jane.

"What do you think, the boys backed out, we're alone in this." Wynifred said with slight fear in her voice.

"When do we graduate?" Jane whispered back with the smell of olives on her breath.

"We have all our hours." Wynifred said softly. "All we have to do is show up for the ceremony and get our diplomas."

Jane nodded.

"When is the next ship out of here?" Jane said slightly slurring her words.

"Friday at 0800 hours." Pike said smiling. "I assume I'll see you there."

"You'll see me at least," Jane said turning her head toward Wynifred. "I don't know about her."

* * *

><p>Pike waited in transport area for Wynifred and Jane. It was 0745 hours and he was about to board a transport when Jane pulled up on a motor bike.<p>

"Ah you're early." Pike said as he watched her park her bike and hand the keys to a small guy.

"I'm always early for departures," Jane said shouldering her bag. "That way I don't have to spend hours on good-byes."

"Where's your friend?" Pike asked looking her in the eyes.

"She backed out," Jane said shifting. "She's the settling type anyway. She decided to settle down the her new fiance Thomas."

"Well, Starfleet is lucky to have you." Pike said smiling.

Jane nodded and tilted her head.

"You say Kirk cheated the Kobayashi Maru test?" Jane said quirking a brow. "Well I'm going to beat it."

Pike chuckled as she got on the ship. Jim walked up from behind a nearby ship.

"She does realize that the Kobayashi Maru is unbeatable right?" Jim asked folding his arms.

"Apparently not," Pike said looking up at Jim. "But she did get McCoy to eat a calzone, so who knows, maybe she can beat it."

"I can hear you." Bones said walking up to Pike. "I only act like an old man, I don't hear like one!"

Jim smiled and helped Pike onto a transport.

"One thing," Jim said looking at Bones then Pike. "When she takes her test, I want to be there for it."

Pike rolled his eyes as they took off.


	3. Chapter 3

**Could Have, Should Have, I'm Glad I Did That**

_Disclaimer: I do not own Star Trek; I do not own the Gene Rodenberry, or the J.J. Abrams version. This is the J.J. Abrams version, but again I do not own Star Trek or anything affiliated with Star Trek or the before mentioned Parties. This is a work of pure entertainment and I am not making any profit from this. The characters belong to Gene Rodenberry and J.J. Abrams and are their respective properties. Please do not sue me._

_Three Years Later:_

* * *

><p>Bones was making his usual rounds around the sick bay when Nurse Chapel walked tiredly over to him.<p>

"Nurse you're not even an hour into you shift and you look exhausted," Bones said folding his arms over his chest and looking at her with some concern. "What's wrong?"

"Nothing was wrong," Nurse Chapel said frowning as she turned to look behind her. "Until Jim decided to take a tour of the botany lab-"

"Allergic reaction?" Bones interrupted tiredly.

"Severe allergic reaction." Nurse Chapel said as she subconciously walked toward Jim. "It's the third time this month."

Bones only heard severe allergic reaction and began preparing a series of hypospays for the young captain. It really annoyed him that Jim was so damned reckless and injury prone. It was bad enough that Jim insisted on going on every dangerous away mission possible, it was even worse that he had to drag McCoy along, but the worst possible thing was that Jim was allergic to nearly every damned thing he touched! You name it and Jim was probably allergic to it! Cats, certain kinds of fabric softener, peanuts, figs, sulphur based medications, Andorian roses, Earth orchids, Vulcan Blueberries (or something they call blueberries, damn things taste like fermented grapes), occular correction drops, mud fleas vaccine, Vulcan mumps vaccines, and this is just what he can name off hand!

"Damn it Jim!" Bones said as he put the hypospray up to Jim's neck. "How many times do I have to tell you to not touch things you know nothing about?"

"How was I supposed to know that an Orion Tulip would do this?" Jim said through severly swollen lips.

"You should know," Bones said pratically stabbing Jim with the next hypo spray. "Because you are allergic to every damned thing in the universe!"

"Not true," Jim said trying to sound indignant. "I'm not allergic to apples."

"Give it time Jim," Bones said stabbing Jim with another hypospray. "You'll be allergic to some form of apple soon."

"Ass." Jim said as he felt the swelling in his lips go down. "Apples are one of the few things I like that I can eat."

Bones sighed and stuck his friend again.

"You know what I enjoy Jim?" Bones said putting his hands on his friends shoulders. "I enjoy not having to worry about what my infantile dumbass friend and captain has gotten himself into this time."

Jim quirked a brow and Bones stuck him in the neck again.

"You are staying over night," Bones said reciting the whole bit from memory and experience. "I don't care if you have "captain-y" things to do, you should have thought about that before putting your face infront of strange plants."

Jim was about to protest when Bones stuck him in the neck again.

"Take a nap Jim." Bones said walking away as Jim fell back onto the bio-bed.

Nurse Chapel looked at Bones with grin.

"I think you get a sadistic glee from hitting him with the hypo sprays." Nurse Chapel said folding her arms.

"Jim has his apples," Bones said with a look that shouted 'well as a matter of fact'. "I have my hyposprays, and I dare anyone to take them away from me."

Nurse Chapel smiled and looked at him.

"You really need to find a better hobby," Nurse Chapel said walking away. "Jim may get wise and stop touching strange plants one day."

"Like that will ever happen." Bones said folding his arms as Chapel walked out.

He walked into his office and sighed as he sat down. Jim was a handful but Chapel was right. Jim will learn how to not stick his face in wierd plants and then what use is his hobby if Jim isn't in sick bay? He shook his head and began filling out medical reports before his shift ended.

Jim woke up to the feeling of annoying bio-bed beneath him. He quickly sat up and look around then down at his hands.

"Swelling went down," He said rubbing his hair and hopping off of the bed. "Hives are gone and so is Bones."

He looked around for a moment and grinned when he heard Bones singing an old Earth song in his office. Jim silently walked over to the door. Bones' accent really came out when he was singing, so Bones never sang in public. Jim though found Bones' music atrocious but hearing Bones sing was priceless. It made Bones sound like a happy individual and not a grumpy and bitter divorecee.

"Hello Bones!" Jim said loudly in the door way.

"Damn it Jim!" Bones said tossing his PADD out of shock. "Knock first you damned infant!"

"But I love hearing you sing!" Jim said with a shit eating grin.

"I hate having you pop up like a damned gofer!" Bones said with a small frown.

Jim rolled his eyes and let himself into Bones' office.

"Guess what," Jim said sitting on the desk. "Bones, guess what Bones."

Bones tried to ignore Jim but the damned infant began waving his hand in front of Bones' PADD. Bones tried moving but Jim moved with him.

"Damn it Jim what?" Bones shouted in frustration.

Jim grinned like a toddler who had a frog hidden in his pocket.

"She's taking the test." Jim said smiling.

Bones looked at Jim for a moment.

"Jim," Bones said putting the PADD down. "Let's pretend that I've only been working all day, that in the past week I've only had 6 hours of sleep total and it's thursday, let's pretend that I'm tired and that my brain isn't exactly going on full warp. "

Jim gave a small chuckle and gave Bones a slap on the back.

"Jane," Jim said smiling. "Jane is taking the Kobayashi Maru, and we are going to see her take it."

"Why would we go and watch her take a test that she has no chance of passing?" Bones asked quirking his brow.

"Because," Jim said smiling. "I kinda told her we would."

"I won't go." Bones said folding his arms.

"Yes you will." Jim said spinning Bones' chair with Bones in it. "And you'll be happy to see her."

Bones looked up at Jim defiantly.

"James Tiberius Kirk," Bones said with his Georgia boy accent coming out full force. "I ain't going to watch her take that damned test and that's final!"

* * *

><p>Bones stood looking down into the familiar simulator that he had been in with Jim those six years back.<p>

"Not much has changed has it?" Jim said looking down into the simulator.

Bones stayed silent and looked down into the viewing room. He was still mad at Jim for making him go watch Jane fail. Bones wasn't upset about Jim making him watch **Jane** fail; the fact was he hated watching anybody fail. He looked down and saw a young woman with a short ponytail walk in and sit in the captain's chair.

"She's here, and some of her crew follows," Jim narrated as the cadets walked in. "What's this? She's short two crewman, let's volunteer!"

Bones frowned.

"Damn it Jim, no!" Bones said as Jim dragged him toward the simulation room. "I'm not helping her fail-"

"I'm not going to fail ," Jane said coolly from the captain's chair. "McCoy you man communications, Kirk you have the helm."

McCoy looked at her and raised his eyebrows.

"And who do you think you are?" McCoy asked with a quirked brow.

"Right now in this simulator," Jane replied standing up. "I'm your captain, and you are my communications officer, now please sit down before I have you removed from the bridge."

"Listen here missy," Bones said pointing his index finger in her face. "I don't care what you think you are in this simulator, but you're still a cadet-"

She grabbed his finger and bent it back and made Bones yell out in pain.

"Get that over-washed finger out of my face," Jane said looking him directly in the eye as he bent over in pain. "Or I break it off and get it out of my face for you!"

Jim looked at the scene and let out a sudden laugh. He didn't want to see his friend injured, but she was at least a foot shorter than he was and she was bringing this gruff country doctor to his knees.

"LET GO OF ME WOMAN!" Bones shouted in pain.

"I can't hear you." She said as she held his index finger firmly in place.

"Let go of me you HELL BITCH!" McCoy yelled out as she looked at him with pleased glee.

"Hell bitch what?" She asked grinning from ear to ear as McCoy glared daggers at her.

"LET GO OF ME CAPTAIN HELL BITCH!" McCoy shouted in pain.

"Thank you Dr. McCoy." She said smiling sweetly.

"Kiss my ass." He said sitting down.

"Not while I'm on duty." Jane said with a sarcastic grin.

Kirk laughed as he watch the pair share a series of snips and snarks before the simulation began.

"Can we please start the test before they start making out!" Jim shouted gleefully at the two way window.

Leonard and Jane looked at Jim.

"Damned infant!" Bones said turning to his station.

"Grow up dumbass." Jane said looking up and signaling the instructors to begin the test.

"You first." Jim snipped as the simulation began.

"Captain," Bones said turning and facing Jane. "We are recieving a distress signal from the Kobayashi Maru, they are stranded and life support is failing, they have landed on an asteriod in the Neutral Zone."

"Contact Medical tell them to prepare for on coming passengers," Jane said stone faced. "We're going to rescue them."

"But it's illegal to enter the Neutral Zone," Jim said with a smirk. "Captain."

"Noted," Jane said stone faced. "If any person wishes to leave do it now. Kirk, send out a ship wide announcement, all non-essential crew and personnel will evacuate by Captain's orders I repeat a mandatory evacuation is required of all non-essential crew and personnel, I want minimal casualities."

Bones and Kirk looked at her for a moment and noticed that the rest of the "crew" did the same.

"Aye Captain," Jim said hitting the comm. "By orders of Captain Ryan, all non-essential personnel and crew are to evacuate immediately, I repeat by orders of Captain Ryan all non-essential personnel and crew are to evacuate immediately."

She tapped her fingers on the captain's chair and looked at the view looked at the navigators and everyone could see her wheels turning.

"Kirk," She said standing up. "Tell the evacuees to load fifty transports light, then tell engineering to prepare for warp."

"What?" Jim asked looking at her as if she were crazy.

"I said Kirk," She repeated flatly. "Load fifty transports light and prepare for warp."

"Aye Captain." Jim said relaying the command.

"Now I want you to do this," She said getting up out of the Captain's chair and over to the helm. "Don't ask just do. Okay?"

Kirk nodded as he and the cadet next to him entered and sent information to various parts of the ship.

* * *

><p>Spock looked on in intrigue as Ensign Ryan took command and Admiral Barton looked on with him.<p>

"What is she doing?" Admiral Barton asked folding his arms behind his back.

"I do not know." Spock responded as he watched the commands being input into the simulator.

He looked at her commands and his brow went up.

"Admiral Barton," Spock asked looking at his commanding officer. "Are you familiar with Montgomery Scott's theory on dematerialization transport at warp speeds?"

"No," Admiral Barton said looking at the screen with renewed interest. "Why?"

"Cadet Ryan is quite familiar with the concept," Spock replied watching the screen. "Perhaps more familiar with the work than Mr. Scott."

Spock and Admiral Barton looked on as the simulation made a loop at warp around the asteroid and rushed past the Kobayashi Maru. Spock looked at the computer and saw that the passengers were safely on board the ship, but then when the ship went back into Federation Space the crew of the Maru were then transported to the escape ships.

"Tell the transport ships to go NOW!" Jane yelled as the Klingons started firing.

The ship returned fire on the Klingons until Jane was assured that the transports were far enough way to prevent any damage to the fleeing transport ships. She looked at her crew and sighed.

"Captain," Kirk said monitoring the console. "The Klingons are pursuing the transports!"

"Tell engineering to eject the warp core and fire on my mark." She said looking at the screen.

"Captain that will kill us!" Kirk said looking at her.

"A skeleton crew of 150 die or a full crew of 750 die plus the crew of the Maru," Jane said sternly. "Eject the damned warp core and fire on my mark!"

"Fire!" Jane shouted as the warp core floated away.

The core ejects and the blast kills the Klingon ships and destroys the ships that Jane commanded, but the crew of the Maru and the 750 people on the transports made it safely away.

"End simulation," Spock said walking down toward Jane. "Explain yourself cadet."

She looked at him for a moment and tapped her nose.

"I was thinking that if a majority of the crew survived plus the Maru survivors then the mission was successful." She said moving her index finger from the tip of her nose to her lip. "Was it?"

"The mission was successful," Spock replied. "Casualties minimal, and the Maru crew saved, what may I ask inspired such an action?"

"Inspired?" She replied looking at him as if she just realized he was there. "I just thought of it off the top of my head."

"Fascinating," Spock responded raising an eyebrow. "You would have us believe that this scenario was thought of suddenly?"

"It was either that or reprogram the simulation," She said smiling. "And I never steal another persons work so I thought of this at the last minute."

She smiled and patted Spock on the shoulder as she walked out. Bones smiled as he watched her leave.

"Gotta give it to her," Bones said slapping Spock on the back. "She is one of a kind."

Spock watched in curiosity as Bones walked out after Jane.

Bones caught up with her at the entrance to the female dorms.

"Hey kid!" He yelled out to her. "Hey kid!"

She turned to look at him and smiled.

"Dr. McCoy," She said walking over to meet him. "How have you been?"

"I've been good," She said smiling. "You look like you been doing well."

"Yeah well chasing Jim around the ship keeps me pretty trim," He said squinting against the sun. "So, Long hair now?"

"Yeah," She said touching her pony tail. "I was just too lazy to have it cut."

She and Bones stood in awkward silence until Jim ran up.

"Flirting much?" Jim asked with a childish grin.

"I was asking Ms. Ryan here how she has been doing," Bones said in a surly manner. "I leave the flirting to infants like you."

"Come on Bones," Jim said putting and arm on Bone's shoulder. "Who wouldn't flirt with her, shoulder length chestnut hair, small waist, wide hips, busty, no more facial piercings."

"I'm standing right here you ass hole." She said looking at Jim.

"I admire God's work when I see it, " Jim replied grinning. "Spock is impressed which is saying something, so I was wondering if you and any of your friends or boyfriends or girlfriends would like to come."

"My friends are going home for the weekend and as for significant others," She said looking tiredly at Jim. "I don't have one because until I'm secure in my Starfleet Career, I refuse to as much as date."

"Really?" Jim said looking at Bones. "Because we need a pilot for the gamma shift and Spock and I think you should be that pilot."

She looked at Jim for a moment.

"Seriously?" She said looking at Jim. "Me a pilot on the best ship in the Fleet?"

"Yep," He said looking between her and Bones. "You will be a pilot for the best ship in all of Starfleet."

"Well then," She said smiling. "I guess I could stand to get shit faced tonight."

* * *

><p>"One tequila, two tequila, three tequila, floor!" Bones, Jim, Jane, and Scotty yelled before taking a shot of the Spanish liquor.<p>

They licked the salt and ate the lime.

"Here's to finding a new pilot for gamma shift and wondering how the hell Scotty managed to find us here!" Jim said raising his shot glass for another round.

"Here, here!" They shouted. "One tequila, two tequila, three tequila, FLOOR!"

They took their third shot of tequila.

"You know," Bones said starting to feel a slight buzz. "There is an old song that says tequila makes her clothes fall off."

"I heard of that," Jane said leaning against the bar. "Let's see how many of these it takes to make my clothes fall off!"

"Bet mine fall off first!" Jim said smiling.

"You're both full of shit!" Leonard said slurring his words as he took another shot. "No one is going to fall out of their clothes!"

_Two shots and thirty minutes later._

Bones and Jane stumbled out of the cab.

"You are drunk." Bones said steadying Jane. "I'm gonna take you back to your room."

"Okay." She said wrapping and arm around his waist. "You smell nice."

"You do to," He said swiping his card on his apartment door. "You stays with me tonight darlin'."

"Alright sugar." She said putting her other arm around him.

"You are very odd." He said opening the door to his room.

"You are very grumpy." She slurred out with a smile.

He put her on his bed and went to the bathroom. He took his shirt off and put on a pair of pajama pants. He looked in the mirror then used the toilet. He washed his hands and walked out to see her laying naked on his bed.

"Only took six shots to get you naked?" Bones slurred out.

"I'm not naked!" She said staggering up. "I'm still wearing my socks!"

He kissed her passionately and lead her to lay on the bed;however, the sudden change of position caused them both to pass out.


	4. Chapter 4

**Could Have, Should Have, I'm Glad I did That**

_**Disclaimers: I don not own Gene Rodenberry, or the J.J. Abrams version of Star Trek, but then again I do not own Star Trek or anything affiliated with Star Trek or the before mentioned parties. This is a work of pure entertainment and I am not making any profit from this writing. The character belong to Gene Rodenberry and J. J. Abrams and are the respective owners property. Please do not sue**_

She woke up to a knee poking her in the back. She rolled over and let out a small gasp.

"Holy shit!" She whispered. "I really did get shit faced!"

She looked under the blankets. He was still wearing pants, but she was naked. She closed her eyes and remembered she just passed out after they made out.

"Oh dear God!" She said trying not to wake the man next to her. "We made out! Oh my God! I am whorish drunk!"

Bones snorted and rolled over. She stood stone still as he went back to sleep.

"Oh what have I done! People are going to call me a gold digger now!" She said to herself as she gathered her clothes. "All I have done to make my own way! This is how I screw it up!"

Bones was looking blindly for the blanket while Jane was looking for her clothes. He opened his eyes when he couldn't find the warmth of his blankets. Jane was bent over wearing a lacy thong.

"Holy shit!" Bones yelled falling out of his bed.

Jane looked back quickly and her entire body turned with her. She had only managed to find her panties.

"We did not have sex," She said holding a sock in one hand and a shoe in the other. "That much I remember!"

Bones looked at her in complete shock.

"Is that what you under your pants!" Bones said looking over the bed from the floor. "Your ass will freeze in the winter time!"

She looked at him and threw the shoe at him.

"My ass should be the least of your worries!" She said looking for the rest of her clothes. "Damn I can hide things when I am drunk!"

Bones was about to reply when he heard a knock at the door. Bones and Jane looked at each other and froze. Bones jumped up off of the floor and dragged her into the bathroom.

"Stay here," He whispered before closing the door. "Who is it?"

"Let me in Bones!" Jim yelled from the other side. "I have to pee!"

Bones froze and grabbed Jane out of the bathroom.

"Under the bed and don't make a sound!" He said pushing her under the bed. "Let me get decent Jim!"

"I have seen penises before Bones I have to pee let me in!" Jim yelled obnoxiously.

Bones opened the door and saw Jim grinning like an idiot.

"You don't have to pee do you?" Bones asked looking Jim in the eyes.

"Nope. I was just wondering how long it would take you to hide her." Jim said walking toward the bed and lifting the blankets to see her. "Thong? Me likey!"

"Go to hell!" She said sliding from under the bed. "Captain. Nothing happened here! We passed out before we went too far."

"Too bad," Jim said looking her over. "I think Bones would be a very happy man if he had a piece of you."

Bones saw Jane's eyes flash with indignant rage. He wasn't even able to stop the inevitable. Jim got a knee to the stomach, an elbow to the jaw, and knee to the face.

"Damn it Jim!" Bones said walking slowly over to his friend. "You had to go one step to far!"

Jim looked up at him and groaned."Ow. My everything!" Jim said rolling over onto his side.

Jane raises her hand up to hit him with her shoe, but Bones grabs both of her arms and now Jim has a full frontal view.

Jim smiles and looks at her. "Pain... So... Worth IT!" He smiled as she moved around causing her breasts to bounce. "Can't feel pain. Can't feel brain."

"Let go of me you dirty old doctor!" She said managing to turn and face McCoy.

He looked at her then by primal mating instinct he looked down at her body and the next thing he remember is a feeling of being headbutted.

"I swear all men think about is sex!" She shouts finding her remaining clothes. "Lord help me! I get drunk and wake up next to a pervert and then his nymphomaniac friend drops by, I am sick of this shit! This is why I always get shit-faced alone!" She put her clothes on and was about to walk out the door when Bones woke up.

"In order to be a gold digger," Bones said rubbing his head. "The old pervert you sleep with has to have money first!"

She stared at him with eyes filled with anger. "I don't need a man to support me! I will make my own way!"

Bones watched as she stormed out of the apartment. "You always bring joy with you appearance Jim." Bones said getting some ice. "Any particular reason you are here?"

Jim smiled sheepishly. "You left your belt in the bar."

Bones looked at the belt then at Jim. "Where did you find it in the bar?"

Jim looked at his friend and gave his signature smart ass grin. "In the chair next to where you were sitting. Let me put it to you in two words. LAP. DANCE. Who knew that for someone with knee problems she could move like that. You two were drunk enough to do sexy dances, but not drunk enough for sex."

Bones looked at the belt and snatched it from Jim. "Leave now." Bones said shoving Jim out the door and closing the door in his captain's face. He goes to the bathroom and looks in the mirror.

_I could have had unprotected sex with a woman almost half my age. I should have know better. _ He sighs as these words run through his mind, but he turns to see her pony tail holder on the night stand. _Maybe it wouldn't have been that bad, there are "plan B" procedures. _


End file.
